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    Chemistry

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    Also known as: Ursodiol, 128-13-2, Actigall, Ursodeoxycholate, Udca, Ursofalk
    Molecular Formula
    C24H40O4
    Molecular Weight
    392.6  g/mol
    InChI Key
    RUDATBOHQWOJDD-UZVSRGJWSA-N
    FDA UNII
    724L30Y2QR
    Ursodeoxycholic Acid
    An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.
    Ursodiol is a Bile Acid.
    1 2D Structure

    Ursodeoxycholic Acid

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
    2.1.2 InChI
    InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
    2.1.3 InChI Key
    RUDATBOHQWOJDD-UZVSRGJWSA-N
    2.1.4 Canonical SMILES
    CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
    2.1.5 Isomeric SMILES
    C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    724L30Y2QR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3 Alpha,7 Beta Dihydroxy 5 Beta Cholan 24 Oic Acid

    2. 3 Alpha,7 Beta-dihydroxy-5 Beta-cholan-24-oic Acid

    3. Acid, Deoxyursocholic

    4. Acid, Ursacholic

    5. Acid, Ursodeoxycholic

    6. Cholit-ursan

    7. Cholofalk

    8. Delursan

    9. Deoxyursocholic Acid

    10. Destolit

    11. Sodium Ursodeoxycholate

    12. Urdox

    13. Ursacholic Acid

    14. Urso

    15. Urso Heumann

    16. Ursobilane

    17. Ursochol

    18. Ursodeoxycholate, Sodium

    19. Ursodiol

    20. Ursofalk

    21. Ursogal

    22. Ursolite

    23. Ursolvan

    2.3.2 Depositor-Supplied Synonyms

    1. Ursodiol

    2. 128-13-2

    3. Actigall

    4. Ursodeoxycholate

    5. Udca

    6. Ursofalk

    7. Ursolvan

    8. Urso

    9. Delursan

    10. Ursodesoxycholic Acid

    11. Urso Forte

    12. Destolit

    13. Ursochol

    14. Cholit-ursan

    15. Litursol

    16. Solutrat

    17. Ursobilin

    18. Ursodamor

    19. Arsacol

    20. Deursil

    21. Lyeton

    22. Ursacol

    23. Urso Ds

    24. Udcs

    25. 3alpha,7beta-dihydroxy-5beta-cholan-24-oic Acid

    26. Ursosan

    27. Urso 250

    28. 3-alpha,7-beta-dioxycholanic Acid

    29. Ursocholic Acid, Deoxy-

    30. 3-alpha,7-beta-dihydroxycholanic Acid

    31. Ursonorm

    32. Nsc 683769

    33. (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic Acid

    34. 3-alpha,7-beta-dihydroxy-5-beta-cholanoic Acid

    35. Ursodeoxycholicacid

    36. (4r)-4-[(3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic Acid

    37. Nsc 657950

    38. Brn 3219888

    39. 3,7-dihydroxycholan-24-oic Acid

    40. Peptarom

    41. Ursodeoxycholic Acid [inn]

    42. Chembl1551

    43. Mls000028461

    44. Chebi:9907

    45. 724l30y2qr

    46. Nsc-683769

    47. Ursodiol [usan]

    48. Antigall

    49. Smr000058403

    50. Urosiol

    51. Cholan-24-oic Acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.beta.)-

    52. 7-beta-hydroxylithocholic Acid

    53. Ursodexycholic Acid

    54. Acido Ursodeossicolico [italian]

    55. (r)-4-((3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

    56. Acido Ursodeoxicolico

    57. Acido Ursodeossicolico

    58. Acido Ursodeoxicolico [inn-spanish]

    59. Acidum Ursodeoxycholicum [inn-latin]

    60. Acide Ursodesoxycholique

    61. Acide Ursodesoxycholique [inn-french]

    62. Acidum Ursodeoxycholicum

    63. Actigall (tn)

    64. Ursodiol (usp)

    65. (4r)-4-[(1s,2s,5r,7s,9s,10r,11s,14r,15r)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic Acid

    66. Ccris 5502

    67. Urso (tn)

    68. Sr-01000737091

    69. Ursodiol [usan:usp]

    70. Einecs 204-879-3

    71. Mfcd00003680

    72. Ursodexycholate

    73. Paptarom

    74. Udiliv

    75. Desol

    76. Urdes

    77. Unii-724l30y2qr

    78. Urosdesoxycholate

    79. 17-beta-(1-methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol

    80. Ursodeoxycholoc Acid

    81. Urosdesoxycholic Acid

    82. 5beta-cholanic Acid-3alpha,7beta-diol

    83. Ursodiol [inci]

    84. Cholan-24-oic Acid, 3,7-dihydroxy-, (3alpha,5beta,7beta)-

    85. 3alpha,7beta-dihydroxy-5beta-cholanic Acid

    86. Ursodiol [mi]

    87. Ursodiol (actigal Urso)

    88. Ursodiol [vandf]

    89. Prestwick0_000958

    90. Prestwick1_000958

    91. Prestwick2_000958

    92. Prestwick3_000958

    93. U0030

    94. 7a-hydroxylithocholic Acid

    95. Ursodiol [usp-rs]

    96. Ec 204-879-3

    97. U-9000

    98. Schembl27200

    99. Bspbio_000956

    100. 4-10-00-01604 (beilstein Handbook Reference)

    101. 7bet.-hydroxylithocholic Acid

    102. Cid_31401

    103. Mls001066373

    104. Mls002548885

    105. Spbio_003105

    106. Ursodeoxycholic Acid, >=99%

    107. Ursodiol [orange Book]

    108. Bpbio1_001052

    109. Gtpl7104

    110. 7.beta.-hydroxylithocholic Acid

    111. Ursodiol (ursodeoxycholic Acid)

    112. 5-beta-cholan-24-oic Acid, 3-alpha,7-beta-dihydroxy-

    113. Dtxsid6023731

    114. Ursodiol [usp Monograph]

    115. Bdbm53721

    116. (3alpha,5beta,7beta,8xi)-3,7-dihydroxycholan-24-oic Acid

    117. Hms1570p18

    118. Hms2097p18

    119. Hms2233l14

    120. Hms3259a13

    121. Hms3714p18

    122. Ursodeoxycholic Acid (jp17/inn)

    123. Ursodeoxycholic Acid [jan]

    124. 3alpha,7beta-dihydroxycholanic Acid

    125. Act02676

    126. Cholan-24-oic Acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-beta)-

    127. Zinc3914809

    128. 3a,7b-dihydroxy-5b-cholan-24-oate

    129. Lmst04010033

    130. S1643

    131. Ursodeoxycholic Acid [mart.]

    132. Ursodeoxycholic Acid [who-dd]

    133. 5a-cholan-24-oic Acid-3a,7a-diol

    134. Akos015955898

    135. Ccg-220958

    136. Cs-1932

    137. Db01586

    138. Ks-5243

    139. Nc00487

    140. Smp2_000012

    141. 3.alpha.,7.beta.-dihydroxycholanic Acid

    142. 3a,7a-dihydroxy-5a-holan-24-oic Acid

    143. 3a,7b-dihydroxy-5b-cholan-24-oic Acid

    144. Ncgc00179363-01

    145. Ncgc00179363-12

    146. Ac-18919

    147. Cas#128-13-2

    148. Cpd000058403

    149. Hy-13771

    150. Nci60_028904

    151. Ursodeoxycholic Acid [ep Impurity]

    152. Ursodeoxycholic Acid [ep Monograph]

    153. Ab00513977

    154. (3a,5b,7b)-3,7-dihydroxy-cholan-24-oate

    155. 3alpha, 7beta-dihydroxy-5beta-cholanoic Acid

    156. 5bet.-cholan-24-oic Acid-3alp.,7bet.-diol

    157. (3a,5b,7b)-3,7-dihydroxycholan-24-oic Acid

    158. C07880

    159. D00734

    160. ((3a,5b,7b)-3,7-dihydroxycholan-24-oic Acid

    161. (3a,5b,7b)-3,7-dihydroxy-cholan-24-oic Acid

    162. Ab00513977-09

    163. Ab00513977_10

    164. 3alp.,7bet.-dihydroxy-5bet.-cholan-24-oic Acid

    165. A905413

    166. Q241374

    167. 3.alpha.,7.beta.-dihydroxy-5.beta.-cholanic Acid

    168. J-005566

    169. J-650210

    170. Sr-01000737091-3

    171. Sr-01000737091-4

    172. Brd-k15697815-001-16-2

    173. 3.alpha.,7.beta.-dihydroxy-5.beta.-cholan-24-oic Acid

    174. Z2786051717

    175. 3.alpha.,7.beta.-dihydroxy-5b-cholan-24-oic Acid

    176. 5.beta.-cholan-24-oic Acid, 3.alpha.,7.beta.-dihydroxy-

    177. Ursodiol, United States Pharmacopeia (usp) Reference Standard

    178. Ursodeoxycholic Acid, British Pharmacopoeia (bp) Reference Standard

    179. Ursodeoxycholic Acid, European Pharmacopoeia (ep) Reference Standard

    180. 17.beta.-(1-methyl-3-carboxypropyl)etiocholane-3.alpha.,7.beta.-diol

    181. 3,7-dihydroxycholan-24-oic Acid-, (3.alpha.,5.beta.,7.beta.)- #

    182. Ursodeoxycholic Acid, 500 Mug/ml In Methanol, Certified Reference Material

    183. Ursodiol, Pharmaceutical Secondary Standard; Certified Reference Material

    184. Ursodeoxycholic Acid For System Suitability, European Pharmacopoeia (ep) Reference Standard

    185. (4r)-4-[(1s,2s,5r,7s,9s,10r,11s,14r,15r)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,1.011,1]heptadecan-14-yl]pentanoic Acid

    186. (4r)-4-[(3r,5s,7s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7-bis(oxidanyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic Acid

    187. (4r)-4-[(3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]valeric Acid

    188. 108609-27-4

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 392.6 g/mol
    Molecular Formula C24H40O4
    XLogP34.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass392.29265975 g/mol
    Monoisotopic Mass392.29265975 g/mol
    Topological Polar Surface Area77.8 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity605
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 8  
    Drug NameActigall
    Drug LabelActigall is a bile acid available as 300 mg capsules suitable for oral administration.Actigall is ursodiol, USP (ursodeoxycholic acid), a naturally occurring bile acid found in small quantities in normal human bile and in the biles of certain other m...
    Active IngredientUrsodiol
    Dosage FormCapsule
    RouteOral
    Strength300mg
    Market StatusPrescription
    CompanyWatson Pharms

    2 of 8  
    Drug NameUrso 250
    PubMed HealthUrsodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelURSO 250 (ursodiol, 250 mg) is available as a film-coated tablet for oral administration. URSO Forte (ursodiol, 500 mg) is available as a scored film-coated tablet for oral administration. Ursodiol (ursodeoxycholic acid, UDCA) is a naturally occurrin...
    Active IngredientUrsodiol
    Dosage FormTablet
    RouteOral
    Strength250mg
    Market StatusPrescription
    CompanyForest Labs

    3 of 8  
    Drug NameUrso forte
    PubMed HealthUrsodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelURSO 250 (ursodiol, 250 mg) is available as a film-coated tablet for oral administration. URSO Forte (ursodiol, 500 mg) is available as a scored film-coated tablet for oral administration. Ursodiol (ursodeoxycholic acid, UDCA) is a naturally occurrin...
    Active IngredientUrsodiol
    Dosage FormTablet
    RouteOral
    Strength500mg
    Market StatusPrescription
    CompanyForest Labs

    4 of 8  
    Drug NameUrsodiol
    PubMed HealthUrsodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelUrsodiol Capsules, USP are a bile acid available as 300 mg capsules suitable for oral administration.Ursodiol, USP (ursodeoxycholic acid) is a naturally occurring bile acid found in small quantities in normal human bile and in the biles of certain ot...
    Active IngredientUrsodiol
    Dosage FormTablet; Capsule
    RouteOral
    Strength250mg; 500mg; 300mg
    Market StatusPrescription
    CompanyCorepharma; Epic Pharma; Par Pharm; Glenmark Generics; Teva Pharms; Lannett; Mylan; Impax Labs

    5 of 8  
    Drug NameActigall
    Drug LabelActigall is a bile acid available as 300 mg capsules suitable for oral administration.Actigall is ursodiol, USP (ursodeoxycholic acid), a naturally occurring bile acid found in small quantities in normal human bile and in the biles of certain other m...
    Active IngredientUrsodiol
    Dosage FormCapsule
    RouteOral
    Strength300mg
    Market StatusPrescription
    CompanyWatson Pharms

    6 of 8  
    Drug NameUrso 250
    PubMed HealthUrsodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelURSO 250 (ursodiol, 250 mg) is available as a film-coated tablet for oral administration. URSO Forte (ursodiol, 500 mg) is available as a scored film-coated tablet for oral administration. Ursodiol (ursodeoxycholic acid, UDCA) is a naturally occurrin...
    Active IngredientUrsodiol
    Dosage FormTablet
    RouteOral
    Strength250mg
    Market StatusPrescription
    CompanyForest Labs

    7 of 8  
    Drug NameUrso forte
    PubMed HealthUrsodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelURSO 250 (ursodiol, 250 mg) is available as a film-coated tablet for oral administration. URSO Forte (ursodiol, 500 mg) is available as a scored film-coated tablet for oral administration. Ursodiol (ursodeoxycholic acid, UDCA) is a naturally occurrin...
    Active IngredientUrsodiol
    Dosage FormTablet
    RouteOral
    Strength500mg
    Market StatusPrescription
    CompanyForest Labs

    8 of 8  
    Drug NameUrsodiol
    PubMed HealthUrsodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelUrsodiol Capsules, USP are a bile acid available as 300 mg capsules suitable for oral administration.Ursodiol, USP (ursodeoxycholic acid) is a naturally occurring bile acid found in small quantities in normal human bile and in the biles of certain ot...
    Active IngredientUrsodiol
    Dosage FormTablet; Capsule
    RouteOral
    Strength250mg; 500mg; 300mg
    Market StatusPrescription
    CompanyCorepharma; Epic Pharma; Par Pharm; Glenmark Generics; Teva Pharms; Lannett; Mylan; Impax Labs

    4.2 Drug Indication

    The drug decreases the absorption of cholesterol and is used to dissolve (cholesterol) gallstones in patients as an alternative to a surgical procedure to remove the gallstones.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ursodiol (commonly known as ursodeoxycholic acid) is a product of metabolism of bacteria in the intestine. It is considered a secondary bile acid. The other type of bile acid, primary bile acids, are produced hepatically and subsequently stored in the gallbladder. When primary bile acids are secreted into the large intestine, they can be broken down into secondary bile acids by bacteria present in the intestine. Both types of bile acids assist in the metabolism of dietary fat. Ursodeoxycholic acid regulates cholesterol levels by slowing the rate at which the intestine is able to absorb cholesterol and also acts to break down micelles, which contain cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.

    5.2 MeSH Pharmacological Classification

    Cholagogues and Choleretics

    Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    URSODIOL
    5.3.2 FDA UNII
    724L30Y2QR
    5.3.3 Pharmacological Classes
    Bile Acids and Salts [CS]; Bile Acid [EPC]
    5.4 ATC Code

    A05AA02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    A - Alimentary tract and metabolism

    A05 - Bile and liver therapy

    A05A - Bile therapy

    A05AA - Bile acids and derivatives

    A05AA02 - Ursodeoxycholic acid

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Only small quantities of ursodiol appear in the systemic circulation and very small amounts are excreted into urine. Eighty percent of lithocholic acid formed in the small bowel is excreted in the feces, but the 20% that is absorbed is sulfated at the 3-hydroxyl group in the liver to relatively insoluble lithocholyl conjugates which are excreted into bile and lost in feces.

    5.6 Mechanism of Action

    Ursodeoxycholic acid reduces elevated liver enzyme levels by facilitating bile flow through the liver and protecting liver cells. The main mechanism if anticholelithic. Although the exact process of ursodiol's anticholelithic action is not completely understood, it is thought that the drug is concentrated in bile and decreases biliary cholesterol by suppressing hepatic synthesis and secretion of cholesterol and by inhibiting its intestinal absorption. The reduced cholesterol saturation permits the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution.

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    04-Jan-2021
    26-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    (USD/KGS)    		 Number of Transactions

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    DOSAGE - CAPSULE;ORAL - 300MG

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